Travel writers don’t spend much time waxing poetic on the joys of American suburbia – and for good reason. Spending time in the suburbs of most American cities is about as exciting as listening to a filibuster attempt on C-Span. Unless you enjoy the numbing sensation that comes from driving past row upon row of characterless houses, strip malls as far as the eye can see and the identical array of chain stores and restaurants one sees all over American suburbia these days.

But Chicago is different. There are plenty of soulless bedroom communities and quite possibly the lamest historic district in the country, but there are also a number of places that are brimming with character and things to do. Most visitors to Chicago never set foot outside the city center and that’s a shame.

If you stay in the city, you’ll miss out on some of Frank Lloyd Wright’s most impressive creations, one of the country’s best independent bookstores, the Bahai Temple, some beautiful beaches and a host of shopping, dining and cultural attractions in very manageable, walkable towns that are accessible via Metra and/or CTA. (But if you prefer a scenic drive, take Sheridan Road up to Chicagoland’s North Shore.)I’ve lived in Evanston and River Forest, so this is a subjective list based upon my experience in the north and west suburban communities that I’ve had an opportunity to explore during my seven years living in the region.

Evanston

This big, diverse community directly north of the city along Lake Michigan belongs on the itinerary of every visitor to Chicago. It’s home to Northwestern University, some 61 structures listed on the National Register of Historic Places, and six sandy beaches. The pedestrian friendly downtown is filled with nice bookstores, cafés, shopping and restaurants and there are beautiful homes scattered among several historic districts within the town. Evanston also has an amazing library, which allows patrons to take out up to 75 books a time (seriously).

Wilmette

Wilmette is another great lakeside community with a terrific old school cinema, and an endearing little downtown that has a Mayberry-esque charm. Business Week rated Wilmette as one of the top ten places to raise a family in the country and it’s also a great place for visitors to take a long walk or bike ride. Don’t leave town without checking out the stunning Bahai Temple on Linden Avenue.

Winnetka

If you drive through Winnetka with a clunky old car, you might get a few funny looks, as this is one of the poshest communities in the Midwest. Right now, there is a 27,000 square foot home on sale for a cool $27 million in town, and there’s also a modest little, 7 bedroom, 11 bath, 15,000 square foot fixer upper at 319 Sheridan Road that comes in at a just under $16 million.

But it’s still worth a visit despite the pretension. Every town should be fortunate enough to have a great little downtown like this one. It’s filled with interesting, independent shops and restaurants. The town also has three nice beaches and its flagship bookstore, the Book Stall, was voted the best independent bookshop in the country by Publisher’s Weekly this year.

Highland Park

This is another exclusive North Shore community that’s worth a visit thanks to its nice downtown and jaw dropping mansions. Michael Jordan and Billy Corgan of the Smashing Pumpkins own homes here and Corgan recently opened up a tea shop in town as well.

Highland Park may have the most expensive home in the region for sale at 2700 Point Lane. In case you’re in the market, it’s a 9 bedroom, 19 bathroom- yes 19 bathrooms, just in case you have a hockey team over and they all have to go at once-32,683 square foot monster priced at $29 million. Oh, and there’s a 15 car garage to boot.

Lake Forest/ Lake Bluff

Lake Forest is another elegant lakefront community oozing with wealth and charm on the North Shore about 30 miles north of Chicago. The downtown has a European flair and boasts some nice restaurants and distinctive retail. Take a drive or a bike ride around the residential neighborhoods surrounding the downtown and you’ll feel like you’re lost in the pages of “The Great Gatsby.” Lake Bluff has a nice beach, a public green and an old time corner store.

In Lake Forest, check out the mansions on North Mayflower Road. At the moment, there’s a 10 bedroom, 16 bath 24,000 square foot home priced to move at $12 million at #405 and a cute little 7 bedroom, 9 bath number at #255 that’s a steal at just under $8 million.

Oak Park & River Forest

Oak Park is a unique, left leaning community due west of the city, accessible via CTA’s green line or Metra, that prizes its diversity and its Frank Lloyd Wright connection. Wright started his career in Oak Park and you can visit his studio and check out a host of homes he built in the area. Oak Park has the largest concentration of FLW homes in the world.

Oak Park is also the birthplace of Ernest Hemingway, and the Hemingway museum , located right around the corner from the Frank Lloyd Wright Studio. Oak Park also has three distinctive retail districts, but the real attractions here are on the side streets, where you’ll find an array of beautiful homes, many in the Prairie or Victorian style.

Due west of Oak Park, River Forest is another distinguished suburb with more Frank Lloyd Wright houses and dozens of other stately homes on huge lots along wide, tree lined streets that are nothing like most planned community suburbs built today. The residential area between Lake and Augusta and Thatcher to Lathrop is filled with classy, unique homes.

Riverside

Riverside is a splendid little community, just south of Oak Park, with a lost in time downtown, an eye-catching water tower, and some noteworthy architecture. The town itself is a National Historic Landmark that was designed by Frederick Law Olmsted as one of the region’s first planned communities.

Elmhurst

This appealing little community in Chicago’s western suburbs is noteworthy for its appealing, pedestrian friendly downtown that has a cool, 1950s feel to it.

La Grange

La Grange is another western suburb with a terrific, old school downtown and some nice old Victorian homes. Less pretentious than nearby Hinsdale, it boasts an awesome BBQ joint and a classic old cinema. La Grange used to have what was quite possibly the country’s most ludicrous marketing campaign. A few years ago, someone had the bright idea to put up banners all over the town with the words, “Ah, La Grange!” One can only hope they didn’t pay an ad agency too much to come up with that clunker.

Naperville

OK, so Naperville has a lot of sprawl, but it’s also got a killer downtown, with a great riverside bike path and a beautiful, huge man-made beach and pool. The area around North Central College is perfect for a nice stroll.

Other Chicago suburbs that are worth a visit: Forest Park (home to loads of bars and a great St. Patrick’s Day celebration), Glen Ellyn, Glencoe, Woodstock, Hinsdale, Wheaton, St. Charles, Geneva, Frankfort, Western Springs, Highwood and Tinley Park.

It’s no secret that Chicago isn’t lacking for great food or bars. But often, the two are mutually exclusive, no matter what city you’re in. Fortunately, as I discovered on a recent visit, Chicago has a wonderfully eclectic mix of new and established hotspots that manage to combine the best of both worlds. Indulge in boutique bourbon, esoteric microbrews, South Australian Shiraz, or meticulously hand-crafted seasonal cocktails, while savoring bar snacks ranging from pub fare and tacos, to elegant small plates and cheese flights.

Below, my picks for holiday snacking and sipping:

Longman & Eagle
Located in the rapidly gentrifying (but still somewhat seedy) Logan Square, this gastropub has become a hit with food-savvy hipsters for a reason. Besides an awe-inspiring selection of bourbon and other boutique spirits, the food simply rocks. An abbreviated bar menu is available between 3-5pm; expect treats like duck rillettes with cornichons and mustard for five bucks a pop. Dinner hour bar menu standouts on my visit included Slagel Family Farms meatballs with creamy polenta, parsley pesto, and fonduta for just six dollars, and tete du cochon with a sunny side-up duck’s egg, pickled shallot, parsley salad, and 5-spice mustard sauce.

[Photo credit: Laurel Miller]Sepia
This gorgeous, moody restaurant, housed in an 1890’s former print shop, is located in the Fulton River District, downtown. It’s a sedate, intimate atmosphere in which to enjoy chef Andrew Zimmerman’s whimsical, locally-sourced cuisine and well-crafted seasonal cocktails. There is a full menu with entrees averaging $28, so my friend and I instead parked ourselves at a cozy little table in the Lounge to make a meal of drinks and starters.

Spendy but unforgettable small plates like chicken-fried sweetbreads with green tomato jam and piccalilli ($14), and pan-roasted sea scallops with popcorn grits and crispy ham hock terrine ($16) are deeply satisfying. Cocktails are a bit on the feminine side, but a great French 75 (Hendrick’s Gin, fresh lemon sour, orange bitters, and demi-sec sparkling rosé; $12) or sour cherry Old Fashioned (house-infused sour cherry Old Overholt Rye, mole bitters, muddled orange, and brandied cherries; $12) is hard to pass up,

Big Star
If whiskey and rowdy honky-tonks are your thang, and you don’t want to devastate your bank account, head to this insanely popular Wicker Park taqueria. You’ll have to duke it out with yet more hipsters (like Seattle, where I live, Chicago has a plague, but they usually congregate with good reason) and local cooks and chefs for a seat, but the reward is luscious, three-dollar pork belly tacos (you really can’t go wrong with any of the offerings), queso fundido, great guacamole and chips, and free squeeze bottles of salsa verde on every table. The whiskey menu is truly staggering, featuring 23 selections from Buffalo Trace Distillery, alone, and $3 select shots every night of the week. The beer, tequila, and mezcal menus aren’t too shabby, either.

ENO, The Intercontinental
You don’t need to be an oenophile or cheese geek to have fun at this wine bar located off the hotel lobby. The focus is on a changing list of pre-selected wine and cheese flights, arranged by category. Whether you like bubbles, rosé, Rhone Valley, Pinot Noir, or want to concentrate on a featured producer, ENO has something for you, for around $13 to $18.

The staff will also cheerfully help you decide what cheese flights (an amazing bargain at $12, for three cheeses, mostarda, olives, Marcona almonds, baguette, and fruit nut bread) to have with your wine, if you’re so inclined. With selections ranging from semi-soft goat’s milk to aged Spanish sheep cheese or Cheddars, it’s a great way to learn, minus any pretense. There are also daily specials inspired by the local Greenmarket; think milk-braised lamb with mint, or roasted beet salad with Capra Honey goat cheese and pistachios.

Tip: ENO is offering a holiday wine and cheese pairing special through February: a bottle of 2003 Ayer Kupp Reisling and a 13 oz. wheel of award-winning dairy Upland Cheese Company’s (WI) newest release, Rush Creek Reserve, for $45. I tasted this hard-to-find cheese yesterday at the cheese shop where I work, and holy @$%!. It’s a satiny, hammy, unctuously rich washed-rind that is the crack of dairy products.

The Girl & The Goat
It’s irrelevant that this bustling, six-month-old industrial-styled bistro in the West Loop is the baby of Top Chef Season 4 winner Stephanie Izard. She’d be packing them in, regardless, with her rustic, soulful, Mediterranean and Asian-influenced cuisine and down-to-earth philosophy. Izard and her forager work closely with a number of local farms that inspire the ever-changing menu of 30 small plates (10 veg, 10 meat, 10 fish), which practically beg for pairings of wine or beer. Speaking of beer, this is the place for trying out new microbrews by the bottle, or indulging in Three Floyds on tap (an artisan craft brewery from Indiana). If the long bar is full, try the communal table or a seat near the wood-burning oven.

Phoenix Lounge, TheWit Hotel
Open since June, this teeny little mezzanine bar is a great people-watching spot, given the floor-to-ceiling glass windows that surround the lobby of one of Chicago’s quirkiest, hippest hotels, minus the attitude. The location on the Loop and next to the river don’t hurt, either. Phoenix, like the rest of the hotel, sports a retro/Art Nouveau/modernist decor, all black and white and magenta, with etched mirrors and chandeliers. Grab a bar table and watch visitors and locals alike swarm the lobby (popular restaurants cibomatto and State and Lake are also in the hotel, as well as the Roof bar, an epicenter of Chicago nightlife). Despite the high ranking on the coolness meter, TheWit’s staff couldn’t be any nicer or more helpful.

Phoenix is all about short and sweet, with an abbreviated, but thoughtful, wine and cocktail list and bar menu. You can go for an in-house drink (all a steep $13), like Good & Evil (house-infused pancetta vodka, Godiva Liqueur, and cream, if you plan on a very short night), or the more refreshing Elevation (house-infused grapefruit vodka, St. Germain Liqueur, grapefruit juice, fresh lemon juice, simple syrup, and ginger ale). Bar snacks such as veal meatballs in a spicy tomato sauce ($10) and tempura rock shrimp with lemon jam and chili aioli ($12) are pricey for what you get, but very tasty, and a great way to celebrate happy hour.

Mercadito
One of the best Bloody Mary’s–here, known as a Bloody Maria–in town can be found at this upscale taqueria chain known for killer cocktails (there are also locations in Miami and New York). Mercadito thoughtfully provides an $18 brunch special labeled as a “hangover cure.” Choose three items from their menu, plus a cocktail. A tall glass of spicy, savory hair of the dog is even better paired with a steaming bowl of posole rojo loaded with barbacoa chicken; huevos rancheros, and juicy tacos al pastor anointed with grilled pineapple and chile de arbol salsa. Your head and stomach will thank you.

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